2-Bromopyridine → HCID 66687133, compound

Participants

Reaction Steps

To a solution of 2-bromopyridine (3.60 g, 22.5 mmol) in THF (100 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 20.0 mL, 22.5 mmol) and stirred for 1.5 h. Added a solution of 1-N-Boc-4-cyanopiperidine (4.60 g, 21.9 mmol) in THF (50 mL) and stirred for 18 h whilst warming to room temperature. The reaction was diluted with water (400 mL) and extracted with EtOAc (2×400 mL). The combined organic extracts were dried over MgSO4, concentrated under vacuum and purified by column chromatography using 0 to 40% EtOAc in hexanes to afford 6 a clear pale yellow oil (1.01 g, 18%); 1H-nmr (400 MHz, CDCl3) δ 8.68 (d, J=5.0 Hz, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.85 (td, J=8.0, 1.5 Hz, 1H), 7.48 (dd, J=8.0, 1.5 Hz, 1H), 4.21-4.07 (m, 2H), 4.02 (tt, J=11.0, 3.5 Hz, 1H), 2.93 (t, J=11.0 Hz, 2H), 1.89 (d, J=9.5 Hz, 2H), 1.71-1.60 (m, 2H), 1.48 (s, 9H); m/z 232.8 [M-tBu].

Provenance & Evidence